Reaktion #3793

Reaktionsgleichung

acetic

(R)-2-amino-2-phenylethanol

N-methyl-N-(trimethylsilyl)acetamide

→

title compound

N-(2-hydroxyl-1-phenylethyl) -benzamide

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe solution was cooled to 0° C. to 5° C.
2. 2
   Sonstigeto precipitate from solution
3. 3
   FiltrationThis solid was collected by filtration
4. 4
   Waschenwashed with 1N HCl, water
5. 5
   Sonstigerecrystallized from dimethylformamide/water

Vorschrift

A slurry of (R)-2-amino-2-phenylethanol (1.0 g, 7.4 mmol) in 50 mL dichloromethane was allowed to stir with N-methyl-N-(trimethylsilyl)acetamide (3.4 mL, 21.1 mmol) until a homogenous solution occured. The solution was cooled to 0° C. to 5° C. and a solution of 2,2'-dithiobis[benzoyl chloride] (1.0 g, 2.9 mmol) in 20 mL dichloromethane was added. The solution was stirred for 2 hours and 1 mL of 50% aqueous acetic was added causing the crude product to precipitate from solution. This solid was collected by filtration, washed with 1N HCl, water, and recrystallized from dimethylformamide/water to afford 1.2 g of the title compound, mp 235°-236° C.

Quelle